After early failures, Orlando Bravo pioneered software buyouts. This was a contrarian move, as the prevailing view was that these companies were either too old or too risky. This niche focus on making unprofitable software businesses viable became the foundation of his firm's success.
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Instead of selling software to traditional industries, a more defensible approach is to build vertically integrated companies. This involves acquiring or starting a business in a non-sexy industry (e.g., a law firm, hospital) and rebuilding its entire operational stack with AI at its core, something a pure software vendor cannot do.
Breakthrough companies often succeed not by iterating endlessly, but by 'planting a flag'—making a strong, often contrarian bet on a core thesis (e.g., email-first media) and relentlessly executing against that vision, even when it's unpopular or lacks momentum.
Contrary to popular belief, successful entrepreneurs are not reckless risk-takers. They are experts at systematically eliminating risk. They validate demand before building, structure deals to minimize capital outlay (e.g., leasing planes), and enter markets with weak competition. Their goal is to win with the least possible exposure.
Initial data suggested the market for design tools was too small to build a large business. Figma's founders bet on the trend that design was becoming a key business differentiator, which would force the market to expand. They focused on building for the trend, not the existing TAM.
Students often believe their target industry is too crowded. Bravo counters this, recalling how a top PE head told him the industry was 'taken' in 1997. He argues the next generation can build bigger firms by ignoring such cyclical pessimism and focusing on execution.
Orlando Bravo's first deals as a young PE professional were a catastrophe, with two going to zero. His mentor, Carl Thoma, gave him a second chance but with a crucial lesson: you can make mistakes, but you cannot make the same *type* of mistakes again.
The most lucrative exit for a startup is often not an IPO, but an M&A deal within an oligopolistic industry. When 3-4 major players exist, they can be forced into an irrational bidding war driven by the fear of a competitor acquiring the asset, leading to outcomes that are even better than going public.
For years, CNX turned down acquisition offers from firms that only wanted to "milk the existing customer base of maintenance" and halt development. They ultimately sold to Izzy Software because it presented an exciting vision for growing the product, not just harvesting it.
Orlando Bravo didn't get a return offer from his internship. Instead of giving up, he sent 500 resumes and cold-called firms, landing his pivotal role just two weeks before graduating. It shows that persistence, not a linear path, is key to breaking into competitive fields.
Seeing an existing successful business is validation, not a deterrent. By copying their current model, you start where they are today, bypassing their years of risky experimentation and learning. The market is large enough for multiple winners.
